Dimethylamine → HCID 59355185, compound

HRID 1770750Notes

Reaction equation

HRID 1770750 reaction equation
CS(O[CH2:6][CH2:7][N:8]1[CH2:12][C:11]([CH3:14])([CH3:13])[NH:10][C:9]1=[O:15])(=O)=O.[CH3:16][NH:17][CH3:18]>O1CCCC1>[CH3:16][N:17]([CH3:18])[CH2:6][CH2:7][N:8]1[CH2:12][C:11]([CH3:14])([CH3:13])[NH:10][C:9]1=[O:15]

Participants

4

Reactant 2

HCID 674Dimethylamine2×HCID 86665540HCID 86665540, compound

Product 1

HCID 59355185HCID 59355185, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a sealed tube, a solution of 2-(4,4-dimethyl-2-oxoimidazolidin-1-yl)ethyl methanesulfonate (500 mg, 2.1 mmol) and dimethyl amine (4.6 mmol) in tetrahydrofuran (2.3 mL) was heated at 60° C. for 5 hours. Additional dimethylamine (1 mL of a 2M tetrahydrofuran solution) was added and the reaction was heated for 3 additional hours. The solution was concentrated to a crude residue under reduced pressure, then dissolved in 5 mL of 1 N HCl. The aqueous solution was washed with dichloromethane, then made basic (pH>8) with sodium carbonate and extracted with dichloromethane twice. The aqueous solution was further adjusted to pH>10 with NaOH, and extracted with twice with dichloromethane. The combined organic fractions were dried over sodium sulfate and concentrated under reduced pressure to give 316 mg of an off-white solid. 1H NMR (CDCl3, 400 MHz) δ 1.30 (s, 6H), 2.27 (s, 6H), 2.41-2.45 (t, 6.8 Hz, 2H) 3.24 (s, 2H), 3.29-3.33 (t, J=6.8 Hz, 2H), 3.51-3.61 (m, 14H), 3.88 (br m, 2H), 7.27-7.29 (d, J=8.1 Hz, 2H), 7.58-7.60 (d, J=8.2 Hz, 2H); LRMS (ESI/APCI) m/z 186 [M+H]+.

Workup

  1. temperaturethe reaction was heated for 3 additional hours
  2. concentrationThe solution was concentrated to a crude residue under reduced pressure
  3. dissolutiondissolved in 5 mL of 1 N HCl
  4. washThe aqueous solution was washed with dichloromethane
  5. extractionextracted with dichloromethane twice
  6. extractionextracted with twice with dichloromethane
  7. dry with materialThe combined organic fractions were dried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0a0ced000a9141628e52fc76185bde75
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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